August 18, 2025

s20e04: A Software Strategy

0.0 Context Setting

I’m starting this on Sunday, 17 August, 2025 in a cafe with a very nice coffee with the full intent of not sending it today, which believe me is a massive step forward.

0.1 Hallway Track

Ho Hallway Tracks are currently scheduled.

1.0 Some Things That Caught My Attention

1.1 A Software Strategy

This one is about the cycle of starting by building something you need, and then having it be replaced by a commodity.

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I’ve written before about how sometimes your software or technology is the thing that needs to be unique about how you do what you do. Or, rather it’s what can be used to make what you do unique -- or better than anyone else.

A regular problem here is that there’s invariably a bit of software that would help in distinguishing, but it comes down to the question of whether you should build it yourself, or whether you should customize it.

I should point out that at one end of the scale, any sufficiently complex job that is pitched as being accomplished via “customizing” existing software ends up being as complex and expensive as just building the damn thing yourself.

But it’s not that simple, people will say, because at least when you’re customizing it you don’t have to have a bunch of software developers on staff, or at least you don’t have to pay for them and keep supporting the thing. This morning my response to that is: eh, bof.

The irritating thing that keeps happening is that people will invent new things to do in new ways with software and then some of those will catch on and then before you know it, the new thing in software has suddenly become a commodity thing.

Some people will look at this and say: what a waste of money! Why should we build a CMS when we can just use Wordpress!

And this is why I think Vox Media is interesting.

A long long time ago in internet time, Vox Media was a bunch of blogs and when they were babies and making blogs they decided to write their own CMS. Writing your own CMS is a phase every software developer goes through ever since the first developer wanted to let other people know what they were thinking.

This CMS was called Chorus. I hear it was good because it let Vox properties do what they needed to do in terms of publishing articles, but also what they needed to do in terms of other things like “selling ads”. Publishing articles is important on the internet because again, you want to distinguish yourself, and part of distinguishing yourself is how you show up. One of the things people got excited about back in the day was cards.

Another thing that happens when you develop and run your own software is that someone somewhere will say: “hey, if this is so good, wouldn’t other people pay for it?” and that is totally a thing that happens with news organizations and content management systems. It never really works out. But I think that is not the main point of this story.

Anyway, after a while -- say just over ten years or so -- Vox decided to switch to WordPress. This was sad, because Chorus was apparently very good and they had invested a lot of money in it, and it felt like custom software losing to commodity software.

But!

A couple weeks ago, Nilay Patel of The Verge announced a secret side project he’d been working on at Vox Media¹.

It’s essentially a bet on... social? Ish? Software to publish stories natively to a feed, in smaller chunks, for things that Aren’t Stories, but are smaller. And it’s launching with SB Nation, which makes sense for a social software product. Sports checks a lot of boxes: lots of people talk about it, and it includes a nice mix of synchronous and asynchronous activity.

And did I mention that lots of people talk about sport? I mean, maybe even more than people scold each other on Bluesky!

The thing is SB Nation Communities, and Ted Han and I got to talk about it with Andrew Losowsky last week on the best-named podcast on the internet².

I’m only going to talk about one of the interesting things here. I’m not going to talk about what SB Nation Communities is, or how it works, in terms of being interesting social software.

What I am going to talk about is how I think this is a great example of managing software development.

1. Build the software you need for a competitive advantage
2. Keep developing that software
3. Over time that functions of that software become commoditized

Then you’ve got a choice: do you switch to the cheaper commodity software?

Some organizations do. They also take the opportunity to outsource all software development. You can then lay off all your software development capacity. It saves money, after all. Why not leave the software making to the people who concentrate on that?

But that’s not what it looks like Vox did. What Vox did was start working on the next thing, the next bet for what would make them distinctive. And that’s this Communities product.

So they start again:

1. Build the software you need for a competitive advantage
2. Keep developing that software
3. Over time the functions of that software become commoditized

This is normal. It is like eating your babies. It is hard to switch to something else, but you evaluate the choice of doing something new against the cost of continuing what you’re doing. It’s undoubtedly effort to migrate content management systems!

I like this because it’s an example of showing how you understand that, and act like, software is a critical competitive advantage.

(Sometimes that software is invisible. Sufficiently advanced Excel spreadsheets are custom software that are a competitive advantage).

You don’t have to use custom, in-house software forever. There probably will be a time when it’s worth it to switch, and one of those reasons is because you need or will benefit from functionality that doesn’t exist yet. But knowing that you could benefit from that, and having a good idea of what that would be -- that’s product strategy and management, which is intrinsic to your business or the mission of your organization. Vox’s behavior is is more like “we don’t just publish news, we know what it is to be part of information on the internet” -- which isn’t just publishing news.

(And also has a lot to do with knowing, learning, and retaining a lot about running healthy communities online).

Anyway. I thought that was interesting.

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2.0 How People Work

Hi, it’s me again with my very own sponsored content: the story about where my workshop How People Work came from.

Last year, after working with a client on three consulting gigs, I was asked if I was willing to put myself out of a job by teaching their senior leads how to “do what you do”.

This was existentially terrifying, and I had to spend a few months finding myself. I’m serious here -- I don’t think, really, about what I’m doing. Helpfully, my client was also able to tell me what they were looking for.

What I did was teach their leads how to be more influential. Being more influential meant a higher chance of doing a good job, of retaining a client, referrals, and better performing teams.

Doing that meant deconstructing what I do to have a good relationship with people, like how to run 1:1s not just with lead clients, but other people involved in pulling off a project well. And in a not-shitty way, because it’s super easy to be gross about “building a relationship with someone”.

Becoming more influential meant teaching people how to read organizations: how and where influence flows and why, how people are motivated as human beings, the different carrots (and when to use sticks). Sticks themselves aren’t themselves punishments. They’re mature conversations about consequences of action and knowing that everybody likes to avoid things that will make them feel bad.

It meant slowing down and teaching people how to talk so that people trust you -- even when, and especially when, you have to give them bad news. Great clients (You can teach clients to be great, but you can’t make them be great) might be disappointed about bad news, but they’d rather hear it so they can make informed decisions. Plus I get to show a slide with Dr. Gregory House in it and about how everyone lies, even a little, even with the best of intentions.

It meant taking a whole week to learn and practice cutting out business bullshit in their writing. You know what I mean, you’ve been taught to do it for the last twenty odd years and it’s so easy it’s unconscious. If you don’t like reading or writing it, it’s reasonable your recipient or audience feels the same way. (Believe me, they do. Even if you think they want and need that bullshit.)

And lastly it meant a week teaching, learning, and applying the fundamentals of strategy: of intentionally making choices to increase your chances of success, and knowing what you want to succeed at. Which, again, is hard. It’s not like people have oodles of spare time. It also wasn’t just about their client’s strategy, but their team strategy as well. Everybody has to make choices, and not making a choice is a choice, too.

This was for a services company, but it’s just as important inside an organization. You need to work with other people and other teams. You need them to understand what you’re saying and what you need, to persuade them to do what you need and know that what you need is the right thing at the right time.

Which is all to say that I wouldn’t be excited to do this with more people. For me, it’s the chance to work with smart people who want to get better at how they work so they can deliver even better work. Or, at least, lead slightly less stressful lives.

If that sounds like it could help someone you know, then it’d be great if you could forward them this. Or maybe you could do with that help?

Reply and drop me a line, or we can have a quick chat, too.

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Hey again.

The sponsored content was longer than the actual content? That feels awkward.

Anyway, how are you doing? I’m doing... OK?

I will leave you with my realization while at dinner with friends that truffle oil is white people MSG.

Best,

Dan

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